EP2318473A1 - Fluorverbrückte assoziate für optoelektronische anwendungen - Google Patents
Fluorverbrückte assoziate für optoelektronische anwendungenInfo
- Publication number
- EP2318473A1 EP2318473A1 EP09777707A EP09777707A EP2318473A1 EP 2318473 A1 EP2318473 A1 EP 2318473A1 EP 09777707 A EP09777707 A EP 09777707A EP 09777707 A EP09777707 A EP 09777707A EP 2318473 A1 EP2318473 A1 EP 2318473A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fluorine
- oligomer
- associate
- injection unit
- bridged
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000005693 optoelectronics Effects 0.000 title claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 126
- 238000002347 injection Methods 0.000 claims abstract description 55
- 239000007924 injection Substances 0.000 claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 33
- 230000005525 hole transport Effects 0.000 claims abstract description 29
- -1 fluoro radicals Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 4
- 230000032258 transport Effects 0.000 description 26
- 239000010410 layer Substances 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 13
- 229920000547 conjugated polymer Polymers 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000005504 styryl group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 229920000265 Polyparaphenylene Polymers 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- 238000003089 Pariser Parr Pople method Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Chemical class C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 239000011159 matrix material Substances 0.000 description 3
- 230000000877 morphologic effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 2
- GODFYRLYJQMVAD-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 Chemical class C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 GODFYRLYJQMVAD-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical class C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 150000002979 perylenes Chemical class 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000002988 phenazines Chemical class 0.000 description 2
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 150000003252 quinoxalines Chemical class 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000005266 side chain polymer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- DBENTMPUKROOOE-UHFFFAOYSA-N 2-naphthalen-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 DBENTMPUKROOOE-UHFFFAOYSA-N 0.000 description 1
- SCXBFXGVOQYURB-UHFFFAOYSA-N 2-phenyl-1h-isoquinoline Chemical compound C1=CC2=CC=CC=C2CN1C1=CC=CC=C1 SCXBFXGVOQYURB-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- XDFUNRTWHPWCKO-UHFFFAOYSA-N 4,5,9,10-tetrahydropyrene Chemical class C1CC2=CC=CC3=C2C2=C1C=CC=C2CC3 XDFUNRTWHPWCKO-UHFFFAOYSA-N 0.000 description 1
- WPCIUCNVWJNRCD-UHFFFAOYSA-N 4,5-dihydropyrene Chemical class C1=CC=C2CCC3=CC=CC4=CC=C1C2=C34 WPCIUCNVWJNRCD-UHFFFAOYSA-N 0.000 description 1
- ZWKIJOPJWWZLDI-UHFFFAOYSA-N 4-fluoro-1h-indole Chemical compound FC1=CC=CC2=C1C=CN2 ZWKIJOPJWWZLDI-UHFFFAOYSA-N 0.000 description 1
- MZCJSUCRGWIKHH-UHFFFAOYSA-N 6,7-dihydrobenzo[d][1]benzoxepine Chemical class O1CCC2=CC=CC=C2C2=CC=CC=C21 MZCJSUCRGWIKHH-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
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- 239000010405 anode material Substances 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a fluorine-bridged associate consisting of an oligomer or polymer containing fluoro radicals attached to the
- Oligomer or polymer backbone and up to three types are selected for the function of various functional units in the backbone selected from the group consisting of a hole transport and / or hole injection unit, an electron transport and / or electron injection unit and an emitter unit, and one to three kinds of the function of various compounds having a fluorine residue selected from a hole transport and / or hole injection unit, an electron transport and / or electron injection unit and an emitter unit, and an optoelectronic device in which the fluorine-bridged associate is used.
- Organic-based charge transport materials for example triarylamine-based hole transports
- OLEDs organic or polymeric light-emitting diodes
- O-SC organic solar cells
- O-FET organic field-effect transistors
- OF-TFT organic thin-film transistors
- O-IC organic switching elements
- O-lasers organic laser diodes
- Electrodes which is often metallic or inorganic, but may also be composed of organic or polymeric conductive materials,
- Planarization layer often formed of one or more conductive doped polymer (s),
- the present invention is particularly, but not exclusively, directed to organic light emitting devices (OLEDs) which are often referred to as polymer light emitting diodes (PLEDs) when polymeric materials are used.
- OLEDs organic light emitting devices
- PLEDs polymer light emitting diodes
- the arrangement described above represents the general structure of an optoelectronic device, wherein different layers can be combined, so that in the simplest case, an arrangement of two electrodes, between which there is an organic layer consists.
- the organic semiconductor layer in this case fulfills all functions, including the emission of light.
- Such a system is described, for example, in WO 90/13148 A1 on the basis of poly (p-phenylenes).
- the polymers for optoelectronic applications that can be used in the above-mentioned organic semiconductor layer are generally conjugated or partially conjugated backbone polymers, the polymer backbone itself playing an important role in optoelectronic properties to form side chain polymers such as polymers eg PVK (poly-N-vinylcarbazole) where the functionality is realized by a transport unit which is chemically bonded to the backbone or by neutral polymers which provide only the film forming properties (as known from organic photoreceptors). at which hole transport materials are typically dissolved in polycarbonate). All of these approaches are in principle operational and are described in the literature.
- PVK poly-N-vinylcarbazole
- Conjugated polymers for opto-electronic applications e.g.
- Polyfluorenes, polyindenofluorenes, polyphenylenes and polyphenylenevinylenes have proven suitable for OLED applications and organic photovoltaic applications.
- the life of the devices, which are made from these polymers has increased steadily over the years, but progress has been slower than "Evaporated small molecule” devices (SMOLED 's).
- the object of the present invention was to develop new optoelectronically functional oligomers or polymers for optoelectronic applications, in particular for OLED applications, which do not have the aforementioned disadvantages of known approaches, and an optoelectronic device, which new, opto-electronically functional oligomers or polymers.
- a fluorine-bridged associate consisting of
- One to three types of functionally different compounds with a fluoro residue consisting of a hole transport and / or hole injection unit, electron transport and / or
- the fluorine-bridged associate according to the invention contains an oligomer or polymer backbone to which fluorine residues are attached, which may be selected from the fluorine radicals mentioned below.
- backbone means that the fluoro radicals can be located directly on the polymer or oligomer backbone or in optional side chains of the polymer or oligomer. optionally up to three types with regard to their function of different functional units for optoelectronic applications, such as a hole transport and / or hole injection unit, an electron transport and / or electron injection unit and an emitter unit Examples of these units are also described below.
- the basic idea of the present invention is to bind to the oligomer or polymer backbone one to three species with respect to their function of different compounds with a fluorine radical by means of fluorophilic interactions, so that a fluorine-bound associate is obtained which has at least part of the functions or even all functions for example, for an organic layer are required in an OLED, i. Hole transport and / or hole injection, electron transport and / or electron injection, and emission.
- These compounds having a fluorine radical can be selected according to the invention from the group consisting of a hole transport and / or hole injection unit, an electron transport and / or electron injection unit and an emitter unit, examples of which are also described below.
- One emitter unit is equivalent to “multiple emitter units”.
- a term in the singular, such as “a” or “a” or “an” etc. in the present invention also includes a plurality thereof unless expressly mentioned otherwise.
- the fluoro-bridged associate of the present invention has the advantage that the functional Optoelectronic functional compounds can be attached to the oligomer or polymer backbone (or side chain) without chemical reactions and positioned at the desired site on the oligomer or polymer backbone (or side chain) and at a desired distance therefrom.
- an electron transport and / or electron injection unit with a fluorine residue is bound by a fluorine residue on the oligomer or polymer backbone at the desired location at a suitable distance from the hole transport unit that the best possible performance of an optoelectronic device containing the fluorine-bridged associate of the present invention is obtained.
- the oligomer or polymer backbone does not comprise a functional unit and the fluoro-bridged associate comprises three types of compounds having a fluoro radical as mentioned above.
- the oligomer or polymer backbone comprises a hole transport and / or hole injection unit and the fluoro-bridged associate preferably has an electron transport and / or electron injection unit and / or an emitter unit as compound (s) with a fluorine residue.
- the oligomer or polymer backbone comprises an electron transport and / or electron injection unit and the fluoro-bridged associate comprises a hole transport and / or hole injection unit and / or an emitter unit as a compound (s) having a fluorine residue.
- the oligomer or polymer backbone comprises an emitter unit and the fluoro-bridged associate comprises a hole transport and / or hole injection unit and / or an electron transport and / or electron injection unit as a compound (s) having a fluorine residue.
- the oligomer or polymer backbone comprises a hole transport and / or hole injection unit and an electron transport and / or
- Electron injection unit and the fluoro-bridged associate one (or more) emitter unit (s) as compound (s) with a fluorine residue.
- the oligomer or polymer backbone comprises a hole transport and / or
- Hole injection unit and an emitter unit and the fluorine-bonded associate an electron transport and / or electron injection unit as a compound (s) with a fluorine residue.
- Oligomer- or polymer backbone an electron transport and / or electron injection unit and an emitter unit and the fluoro-bridged associate a hole transport and / or hole injection unit as a compound (s) with a fluorine residue.
- the functions of the fluorine-bridged association of the present invention can be tailored to the respective application purpose.
- the oligomer or polymer is a non-conjugated or partially conjugated homo- or co-oligomer or polymer.
- Conjugated oligomers or polymers in the context of the present invention are oligomers or polymers which contain in the main chain mainly sp 2 -hybridized (or else sp-hybridized) carbon atoms, which may also be replaced by corresponding heteroatoms. This means in the simplest case, the alternating presence of double and single bonds in the main chain.
- the term "major” means that naturally occurring defects that result in conjugation disruptions are nevertheless covered by the term “conjugated oligomer or polymer.” It does not, however, mean oligomers or polymers that purposely contain incorporated larger amounts of unconjugated segments.
- a polymer or oligomer is also referred to as conjugated, if in the main chain, for example, arylamine units, arylphosphine units and / or heterocycles (ie conjugation via N, O or S atoms) and / or organometallic complexes ( ie conjugation over the metal atom).
- units such as simple (thio) ether bridges, ester linkages, amide or imide linkages are defined as non-conjugated segments in the present invention.
- a partially conjugated oligomer or polymer is to be understood as meaning an oligomer or polymer which contains either in the main chain longer conjugated portions which are interrupted by non-conjugated portions or in the side chains of one non-conjugated in the main chain Polymer contains longer conjugated sections.
- the oligomer or polymer of the present invention is a conjugated homo- or co-oligomer or polymer, wherein the co-oligomer or polymer in another preferred embodiment is a random co-oligomer or polymer conventional co-oligomer or polymer or a block co-oligomer or polymer.
- the oligomer preferably contains 3 to 9 repeat units and the polymer preferably contains more than 9 (ie 10 or more) repeat units.
- the fluoro radicals which can be used according to the invention ie the fluoro radicals which are bonded to the oligomer or polymer backbone and the functional compound, preferably have the general formula C x H y F z , where x> 0, y> 0 and z> 1, and none, one or more CH 2 groups, which may also be adjacent, by O, S, Se, Te 1 Si (R 1 ) 2) Ge (R 1 ) 2) NR 1 , PR 1 , CO, P (R 1 ) O may be replaced, where R 1 is identical or different at each instance and is a straight-chain or branched or cyclic alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl or Heteroalkyl group is, wherein one or more non-adjacent C atoms of the non-aromatic moieties may be replaced by O, S, CO, COO
- the fluoro radicals are selected from the group consisting of F 1 CF 3 , C 2 F 5 , CF 3 (CH 2 ) a S ( CF 3 CF 2 S or (CF 3 - (CH 2 ) a ) 2 N, where a is preferably an integer from 0 to 5.
- a spacer Sp is preferably present in the oligomer or polymer between the oligomer or polymer backbone and the fluorine residues.
- spacer Sp it is possible to use all groups which are known to the person skilled in the art for this purpose.
- Sp is preferably a linear or branched alkylene group having 1 to 20
- Preferred spacer groups are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methylenoxybutylene, ethylenethioethylene, ethylene-N-methyl-iminoethylene, 1-methylalkylene, ethenylene, propenylene or butenylene.
- Sp is an alkyl or alkoxy group having 2 to 8 carbon atoms.
- straight-chain groups are particularly preferred.
- a functional compound By the presence of the spacer Sp between the oligomer or polymer backbone and the fluorine residues, a functional compound can be reacted with a fluoro moiety, e.g. a hole conductor, an electron conductor and an emitter are kept at a distance from the oligomer or polymer backbone so as to obtain optimum performance of the optoelectronic device containing the fluoro-bridged associate.
- a fluoro moiety e.g. a hole conductor, an electron conductor and an emitter are kept at a distance from the oligomer or polymer backbone so as to obtain optimum performance of the optoelectronic device containing the fluoro-bridged associate.
- the emitter is a triplet emitter.
- triplet emitter are often quenched by conjugated regions in the oligomer or polymer backbone that reduce band gap.
- Performance of a corresponding optoelectronic device, in which the fluorine-bound associate is included, can be increased according to the invention.
- oligomer or polymer which can be used in the fluorine-bridged associate of the present invention.
- further repeat units are specified which are used in the oligomers or polymers of the fluorocrosslinked associates according to the invention either as oligomer or polymer backbone units, or in order to give them further special functions.
- preferred polymers or fluorine-containing polymers are conjugated polymers or partially conjugated polymers which contain sp 2 -hybridized carbon atoms in the main chain which may also be replaced by corresponding heteroatoms .
- conjugate is also designated if, for example, arylamine units and / or certain heterocycles (ie conjugation via N, O or S atoms) and / or organometallic complexes (ie conjugation via the metal atom ) are located.
- Typical representatives of conjugated polymers are polyparaphenylenevinylenes (PPV), polyfluorenes, polyspirobifluorenes, polyphenanthrenes, polydihydrophenanthrenes, polyindenofluorenes, systems broadly referred to poly p-phenylenes (PPP) are based, and derivatives of these structures, especially those derivatives having fluorine-containing groups. Particular preference is given according to the invention to those polymers which contain further structural elements and are thus to be referred to as copolymers.
- Group 1 structural units representing the polymer backbone.
- Group 2 structural units which influence the hole injection and / or transport properties of the polymers or serve as a hole injection and / or transport unit.
- Group 3 structural units which influence the electron injection and / or transport properties of the polymers or serve as electron injection and / or transport unit.
- Group 4 Structural units comprising combinations of Group 2 and Group 3 individual units.
- Group 5 structural units which influence the morphological properties and / or the emission color of the resulting polymers or of the fluorine-bridged associate.
- Group 6 structural units which change the emission characteristics to such an extent that electrophosphorescence can be obtained instead of electrofluorescence.
- Group 7 structural units that improve the transition from singlet to triplet state.
- Preferred group 1 units are, in particular, those which contain aromatic or carbocyclic structures having 6 to 40 C atoms.
- Suitable and preferred moieties include fluorene derivatives, e.g. in EP 0842208, WO 99/54385, WO 00/22027, WO 00/22026 and WO 00/46321, indenofluorene derivatives, furthermore spirobifluorene derivatives, e.g. in EP 0707020, EP 0894107 and WO 03/020790, phenanthrene derivatives or dihydrophenanthrene derivatives, e.g. disclosed in WO 2005/014689. It is also possible to use a combination of two or more of these monomer units, e.g. in WO 02/077060.
- Preferred units for the polymer backbone are, in particular, spirobifluorene, indenofluorene, phenanthrene and dihydrophenanthrene derivatives.
- Particularly preferred units of group 1 are divalent units according to the following formulas, in which the dashed lines represent the link to the adjacent units:
- YY is Si or Ge
- W is O, S or Se
- R 2 is identical or different at each occurrence
- H 1 is a straight-chain, branched or cyclic alkyl or alkoxy chain having 1 to 22 carbon atoms, in which also one or more non-adjacent C atoms by O, S 1 CO, O-CO , CO-O or O-CO-O may be replaced, wherein one or more H atoms may be replaced by fluorine, an aryl or Aryloxy group having 5 to 40 carbon atoms, in which also one or more C atoms may be replaced by O, S or N, which may also be substituted by one or more non-aromatic radicals R 2 , or F, CN, N (R 3 ) 2 or B (R 3 ) 2 ; and
- R 3 is the same or different at each occurrence H, a straight-chain, branched or cyclic alkyl chain having 1 to 22 C atoms, in which also one or more non-adjacent C atoms by O, S 1 CO 1 O-CO, CO- O or O-CO-O may be replaced, wherein also one or more H atoms may be replaced by fluorine, or an optionally substituted
- aromatic amines or electron-rich heterocycles e.g. substituted or unsubstituted triarylamines, benzidines, tetraarylene-para-phenylenediamines, phenothiazines,
- HOMO highest occupied molecular orbital
- Particularly preferred units of group 2 are divalent units according to the following formulas, in which, in the case where these units are part of an oligomer or polymer, the dotted lines represent the link to the adjacent units:
- R, 11 has one of the meanings given above for R, the different formulas at the free positions also in addition one or more substituents R 11 can be substituted and the symbols and indices mean the following:
- n is the same or different at every occurrence 0, 1 or 2
- p is identical or different at each occurrence 0, 1 or 2, preferably 0 or 1,
- o is identical or different at each occurrence 1, 2 or 3, preferably 1 or 2,
- Ar 11 , Ar 13 are the same or different at each occurrence and are an aromatic or heteroaromatic ring system having 2 to 40 C atoms, which may be monosubstituted or polysubstituted by R 11 or may also be unsubstituted; the possible substituents R 11 can potentially be located at any free position,
- Ar 12 , Ar 14 are the same or different on each occurrence Ar 11 , Ar 13 or a substituted or unsubstituted stilbenylene or tolanylene unit,
- Ar 15 is identical or different at each occurrence either a system according to Ar 11 or an aromatic or heteroaromatic ring system having 9 to 40 aromatic atoms (C or heteroatoms), which may be monosubstituted or polysubstituted by R 11 or unsubstituted and which at least two condensed rings; the possible substituents R 11 can potentially sit at any free position.
- LUMO lowest unoccupied molecular orbital
- Particularly preferred units of group 3 are divalent units according to the following formulas, in which, in the case where these units are part of an oligomer or polymer, the dotted lines represent the link to the adjacent units:
- Group 4 - Structural units comprising combinations of Group 2 and Group 3 individual units:
- the polymers, or the fluoro-bridged associate according to the invention contain structural units in which structures which enhance hole mobility and which electron mobility are directly bonded to one another or both. However, some of these units shift the emission color to yellow or red. Their use in the optoelectronic device according to the invention for generating blue or green emission is therefore less preferred.
- Group 4 units are included in the polymers, they are preferably selected from divalent units according to the following formulas, wherein, in the case where these units are part of an oligomer or polymer, the dashed lines represent linking to the adjacent units :
- Group 5 - Structural units which influence the morphological properties and / or the emission color of the resulting polymers or compounds with fluorine radicals in the context of the present invention, which fulfill this task:
- these are those which have at least one further aromatic or another conjugated structure which does not fall under the abovementioned groups, ie which only slightly influences the charge carrier mobility, which are not organometallic complexes or which have no influence on the singlet Triplet transition.
- Such structural elements can influence the morphological properties, but also the emission color of the resulting polymers or of the fluorine-bridged associate. Depending on the unit, they can therefore also be used as emitters.
- Preference is given to substituted or unsubstituted aromatic structures having 6 to 40 carbon atoms or else tolan, stilbene or Bisstyrylarylenderivate, each of which may be substituted by one or more radicals R 11 .
- Particularly preferred is the incorporation of 1, 4-phenylene, 1, 4-naphthylene, 1, 4 or 9,10-anthrylene, 1, 6, 2,7- or 4,9-pyrenylene, 3,9- or 3,10-perylenylene, 4,4'-biphenylylene, 4,4 "-terphenylylene, 4,4'-bi-I 1 I 1 -naphthylylene, 4,4'-tolanylene , 4,4'-stilbenylene or 4,4'-bis-styrylarylene derivatives.
- oligomer or polymer backbone - be used e j those which are used as the blue emitter, such as a fluorinated compound according to the invention.
- e j those which are used as the blue emitter, such as a fluorinated compound according to the invention.
- These are generally those that have at least one aromatic or other conjugated structure, but do not shift the emission color to green or red.
- Stilbene and tolan derivatives and certain bis (styryl) arylene derivatives are, for example, the following structural elements which may be substituted or unsubstituted: 1, 4-phenylene, 1, 4-naphthylene, 1, 4 or
- Layer PPPs LPPP
- Ansa structures containing PPPs eg according to EP-A-690086
- Bis (styryl) arylene derivatives which are not electron-rich, can be used for this purpose.
- the oligomer or polymer or fluorine-bridged associate contains green-emitting structural units
- structural units which have at least one aromatic or other conjugated structure and shift the emission color into the green are preferably suitable for this purpose.
- Preferred structures for green emitting units are selected from the groups of the electron-rich bis-styrylarylenes and derivatives of these structures.
- green-emitting structural units are selected from the groups of the benzothiadiazoles and corresponding oxygen derivatives, the quinoxalines, the phenothiazines, the phenoxazines, the dihydrophenazines, the bis (thiophenyl) arylenes, the oligo (thiophenylenes) and the phenazines. It is also permissible for a plurality of such units to be used instead of a green-emitting structural unit, in which case the total proportion of the green-emitting units is not more than 20 mol%, preferably not more than 10 mol% and particularly preferably not more than 3 mol%.
- red-emitting structural units preference is given to units which have at least one aromatic or other conjugated structure and shift the emission color to red.
- Preferred structures for red emitting moieties are those in which electron-rich moieties, such as thiophene, are combined with green-emitting electron-deficient moieties, such as quinoxaline or benzothiadiazole.
- Other preferred red-emitting moieties are systems of at least four fused aromatic moieties, such as rubrene, pentacene or perylenes, which are preferably substituted, or preferably conjugated push-pull systems (systems substituted with donor and acceptor substituents) or Systems such as squarine or quinacridone, which are preferably substituted.
- red-emitting units it is also permissible for a plurality of such units to be used instead of a red-emitting unit, in which case the total proportion of the red-emitting units is not more than 10 mol%, preferably not more than 5 mol% and particularly preferably not more than 1 mol%.
- units which emit light from the triplet state that is to say electrophosphorescence instead of electrofluorescence, are also suitable as blue, green and red emitting structural units, which frequently leads to an increase in energy efficiency. These units are referred to below as the triplet emitter.
- the use of such metal complexes in low molecular weight OLEDs is described, for example, in M.A. Baldo et al. (Appl. Phys. Lett. 1999, 75, 4-6).
- Particularly suitable for this purpose are compounds containing d and f transition metals, which are the o. Fulfill condition. Very particular preference is given here to corresponding structural units which contain elements of group 8 to 10 (i.e., Ru, Os, Rh, Ir, Pd, Pt).
- the colors of the complexes are determined primarily by the metal used, by the exact ligand structure and by the substituents on the ligand. Both green and red emitting complexes are known. For example, an unsubstituted tris (phenylpyridyl) iridium (III) emits green light, while electron-donating substituents para to the coordinating carbon atom (eg, diarylamino substituents) shift the emission to orange-red. Furthermore, derivatives of this complex with varied ligand structure are known, which lead directly (without further substitutions) to orange or deep red emission. Examples of such ligands are 2-phenylisoquinoline, 2-benzothiophenylpyridine or 2-naphthylpyridine.
- Blue-emitting complexes are obtained, for example, by substituting the tris (phenyl-pyridyl) -iridium (III) base with electron-withdrawing substituents such as multiple fluoro and / or cyano groups.
- Preferred fluorescent emitters as compounds having at least one fluoro residue of the present invention are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines and arylamines, each of which is substituted with at least one fluoro group.
- a monostyrylamine is a monostyrylamine.
- a distyrylamine is meant a compound containing two styryl groups and at least one amine, which is preferably aromatic.
- a tristyrylamine is meant a compound containing three styryl groups and at least one amine, which is preferably aromatic.
- a tetrastyrylamine is meant a compound containing four styryl groups and at least one amine, which is preferably aromatic.
- An arylamine or an aromatic amine in the context of the present invention is understood as meaning a compound which has three aromatic or heteroaromatic
- styryl groups are particularly preferably stilbenes, which may also be further substituted on the double bond or on the aromatic. Examples of such compounds are substituted or unsubstituted tristilbeneamines or others
- a phosphorescent emitter compound is preferably selected from the class of metal complexes containing at least one element of atomic number greater than 20, preferably greater than 36 and less than 84, more preferably greater than 56 and less than 80.
- metal complexes comprising copper, molybdenum, tungsten, rhenium, Ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular iridium.
- metal complexes comprising copper, molybdenum, tungsten, rhenium, Ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular iridium.
- phosphorescent materials as used in the prior art.
- Group 6 - Structural units which change the emission characteristics to the extent that electrophosphorescence can be obtained instead of electrofluorescence or compounds with fluorine residues in the sense of the present invention which fulfill this task:
- Preferred structural units of group 6 are those of the following formulas:
- M is Rh or Ir
- Y has the meaning given above, and the various formulas at the free positions by one or
- carbazole and bridged carbazole dimer units are contemplated, e.g. in WO 04/070772 and WO 04/113468.
- ketones, phosphine oxides, sulfoxides and similar compounds such as e.g. in WO 2005/040302 A1.
- the polymer may also further contain metal complexes bound in the main or side chain, which are generally composed of one or more ligands and one or more metal centers.
- the compounds with fluorine residues can also come from this class. Preference is given to polymers which additionally contain one or more structural units selected from groups 1 to 7. Also preferred are fluorine-bridged associates which additionally contain one or more structural units selected from groups 1 to 7.
- the polymers or the fluorine-bridged associate contain structural units which improve the charge transport and / or the charge injection, that is to say structural units from group 2 and / or 3; particularly preferred is a proportion of 1 to 30 mol% of these structural units; very particular preference is given to a proportion of from 2 to 10 mol% of these structural units.
- polymers or the fluorine-bridged associate contain structural units from group 1, structural units from group 2 and / or 3 and structural units from group 5.
- the polymers preferably have from 10 to 10,000, more preferably from 20 to 5,000 and in particular from 50 to 2,000 repeat units. To be distinguished from it are the fluorinated according to invention
- Oligomers having 3 to 9 repeat units may also have all the repeat units defined above, including the emitters.
- the polymers can be linear, branched or crosslinked.
- the copolymers according to the invention may have random, alternating or block-like structures or alternatively have several of these structures in turn. How copolymers having block-like structures can be obtained and which further structural elements are particularly preferred for this purpose are described in detail, for example, in WO 2005/014688. This font is via quote part of the present application.
- the polymers are typically prepared by polymerization of one or more types of monomers. Suitable polymerization reactions are known in the art and described in the literature. Particularly suitable and preferred polymerization and coupling reactions which all lead to C-C linkages are those according to SUZUKI, YAMAMOTO, SILHOE, HECK, NEGISHI, SONOGASHIRA or HIYAMA.
- the C-C linkages are preferably selected from the group of the SUZUKI coupling, the YAMAMOTO coupling and the STILLE coupling.
- a corresponding monomer may be copolymerized with a fluorinated monomer.
- polystyrene resin it may also be preferred not to use the polymer as a pure substance, but as a mixture (blend) together with further optional polymeric, oligomeric, dendritic or low molecular weight substances.
- additional optional polymeric, oligomeric, dendritic or low molecular weight substances can be, for example, the electronic
- the invention further provides solutions and formulations of one or more fluorine-bridged invention
- an optoelectronic device which contains a cathode, an anode and a layer, the layer containing a fluorine-bridged associate according to the invention.
- the optoelectronic device employing the fluorine-bridged associate of the present invention is an organic or polymeric light emitting diode, an organic solar cell (O-SC, e.g., WO 98/48433, WO 94/05045), an organic field effect Transistor (O-TFTs), an organic switching element (O-IC, eg WO 95/31833, WO 99/10939), an organic FeId quench element (, FDQ, eg US 2004/017148 ), an organic optical amplifier, an organic photoreceptor, an organic photodiode, or an organic laser diode (O-LASER, eg, WO 98/03566).
- O-SC organic solar cell
- O-TFTs organic field effect Transistor
- O-IC organic switching element
- O-IC organic switching element
- FeId quench element FDQ, eg US 2004/017148
- O-LASER organic laser diode
- the device is structured, contacted and finally hermetically sealed in a manner known per se, since the service life of such devices is drastically shortened in the presence of water and / or air. It may also be preferred to use a conductive, doped polymer as the electrode material for one or both of the electrodes (electrode and counterelectrode or anode and cathode) and not to introduce an intermediate layer of conductive, doped polymer. For applications in 0-FETs and O-TFTs, it is also necessary that the assembly contains, in addition to the electrode and counter electrode (source and drain), another gate which is surrounded by an insulator layer with a generally high (or rare low)
- Dielectric constant is separated from the organic semiconductor. In addition, it may be useful to bring in the device even more layers.
- the electrodes are chosen in the sense of this invention so that you
- low work function metals, metal alloys or multilayer structures of various metals are preferable, such as alkaline earth metals, alkali metals, main group metals or lanthanides (eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
- alkaline earth metals alkali metals
- main group metals or lanthanides eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.
- further metals which have a relatively high work function such as, for example, B. Ag, which then usually combinations of metals, such as Ca / Ag or Ba / Ag are used. It may also be preferred to introduce between a metallic cathode and the organic semiconductor a thin intermediate layer of a material with a high dielectric constant.
- Suitable examples of this are, for example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides (for example LiF, Li 2 O, BaF 2 , MgO, NaF, etc.).
- the layer thickness of this dielectric layer is preferably between 1 and 10 nm.
- the anode high workfunction materials are preferred.
- the anode has a potential greater than 4.5 eV against vacuum.
- metals with a high redox potential such as Ag, Pt or Au, are suitable for this purpose.
- metal / metal oxide electrodes eg Al / Ni / NiO x , Al / PtO x
- at least one of the electrodes must be transparent be either to allow the irradiation of the organic material (O-SC) or the coupling of light (OLED / PLED, O-LASER).
- a preferred construction uses a transparent anode.
- Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO).
- the polymer P1 according to the invention and the comparative polymer V1 are synthesized by using the following monomers (percentages by mol%) by SUZUKI coupling according to WO 03/048225 A2.
- toluene solutions of polymers P1 and V1 with the inventive emitters T1 and T2 created.
- concentrations are in each case 8% by weight of the emitter relative to the polymer, the total weight 12.5 mg / ml (ie 1 mg / ml T1 or T2 and 11.5 mg / ml P1 or V1).
- Spincoats on quartz slides are used to produce films with a thickness of 80 nm, which are subsequently measured in a PL spectrometer with nitrogen-flooded sample space (Hitachi F-4500 fluorescence spectrometer).
- a measure of the efficient transfer of excitation energy and thus also of an exciton produced by recombination in an OLED from the polymer to the emitter is the ratio of residual emission of the polymer to emitter emission in such a film.
- FIG. 1 shows the spectra of T1 in P1 and T1 in V
- FIG. 2 shows the spectra of T2 in P1 and T2 in V1.
- the excitation wavelength is in each case at the absorption maximum of the polymer at 395 nm. In both cases, the spectra show a higher red content for the likewise fluorinated matrix P1, ie the transmission of the excitation energy works better with the aid of the F-F interaction.
- Table 1 summarizes the results calculated from the normalized spectra and, for simplicity, the ratio of the maxima. Table 1 :
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photovoltaic Devices (AREA)
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Abstract
Description
Claims
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DE102008045663A DE102008045663A1 (de) | 2008-09-03 | 2008-09-03 | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
PCT/EP2009/005707 WO2010025802A1 (de) | 2008-09-03 | 2009-08-06 | Fluorverbrückte assoziate für optoelektronische anwendungen |
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EP2318473A1 true EP2318473A1 (de) | 2011-05-11 |
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US (1) | US9080099B2 (de) |
EP (1) | EP2318473B1 (de) |
JP (1) | JP5778030B2 (de) |
DE (1) | DE102008045663A1 (de) |
WO (1) | WO2010025802A1 (de) |
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DE102009034194A1 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
US20120232238A1 (en) * | 2009-08-03 | 2012-09-13 | The Johns Hopkins University | Ladder-type oligo-p-phenylene-containing copolymers with high open-circuit voltages and ambient photovoltaic activity |
DE102009041289A1 (de) * | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102010009193B4 (de) * | 2010-02-24 | 2022-05-19 | MERCK Patent Gesellschaft mit beschränkter Haftung | Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend |
TWI635111B (zh) * | 2012-03-16 | 2018-09-11 | 馬克專利公司 | 共軛聚合物 |
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- 2009-08-06 EP EP09777707.2A patent/EP2318473B1/de active Active
- 2009-08-06 WO PCT/EP2009/005707 patent/WO2010025802A1/de active Application Filing
- 2009-08-06 US US13/001,910 patent/US9080099B2/en not_active Expired - Fee Related
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DE102008045663A1 (de) | 2010-03-04 |
US20110095283A1 (en) | 2011-04-28 |
EP2318473B1 (de) | 2013-05-29 |
US9080099B2 (en) | 2015-07-14 |
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JP2012502117A (ja) | 2012-01-26 |
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